Compiling Leadership

15 years of building, leading, and managing; failures and successes

05 Jan 2020

Career Growth: Going Forward by Going Backward

One year ago I made a major career change. I transitioned from an engineering director position managing a team of 18 engineers and three managers to an individual contributor senior engineer.

Honestly, I struggled initially while deciding on the transition. It felt like my career would backslide with the change. On one hand, I had fought hard and succeeded to reach the director level and I enjoyed my team - in fact, I had hired almost half of them myself. On the other hand, my team's charter had run its course and the team struggled from a product perspective to find traction. As such, the majority of my efforts went to managing my team through pivots. Every three to six weeks our team would pivot on metrics and product.

It was difficult because I believe it's not a strongly winnable position1. Obviously, management is not a game and there aren't solvable actions, but the idea still applies – there did not seem to be a winnable solution to the problem because there was no way to do well, only to keep my teams’ collective heads above water. After nine months of this, I had enough.

My colleagues, friends, and family were surprised. Okay, that's the understatement of the day - they were floored. Could I seriously make a move from a director to a run-of-the-mill senior engineer? I could count on one hand people who saw my move as anything other than a mistake.

On paper, it would look like a step back. Furthermore, all of my peers and colleagues might look at me as a quitter or failure. To some extent, I think this was true. I noticed certain colleagues postponing or canceling long-standing 1 on 1 meetings. It wasn't all of them but it definitely felt bad.

While five years had passed since I had worked as an individual contributor, I saw lots of opportunities. I knew I could apply my learnings as a founder, manager, and director to my team as an engineer.

These opportunities came quickly mostly because I knew what to look for.

Turning problems into solutions

As an engineering manager, the most difficult situations arise when your team presents a problem with no solution. However, this scenario comes up often and I have gotten pretty good at it2. As I lived the problems my team faced, I could help them understand potential solutions and present them. This has proven massive useful for our team because I can scale my abilities as an engineer by understanding what problems exist and then use my engineering manager abilities to help craft solutions and communicate them.

Communication from junior engineer to executives

As a director, I learned quickly how to convey ideas and drive alignment within my team (all levels of engineers and managers,) as well as to my management chain and executives. The ability to communicate engineering level solutions and problems to any part of the organization allows for us to build a shared vision rather than require coordination3.

For instance, if a senior-level engineer has an idea but doesn't know how to communicate that idea up to senior management. They will need to coordinate with their direct manager and allow time for alignment. Then the two of them will need to coordinate on time to present the idea to senior management.

Short-circuiting the above with the ability to communicate with senior management and executives has allowed our team to scale.

Knowing how to separate the “right” from the “perfect”

As an engineer, it's really hard to not chase a perfect solution. Often this leads to overly abstracted implementations and slower delivery times. Every engineer I know (including me!) does this as a first instinct.

However, the right solution is rarely the perfect solution4. The right solution is frequently the way to deliver an outcome quickly that is good enough to disprove a hypothesis. Applying this thinking as an engineer helps other engineers fight their knee jerk because it's not just management telling engineers to build things differently than their knee jerk.

Going Forward

So one year into this change, applying these learnings and more has been very useful for my team. In fact, I feel like I have excelled more than ever before by combining these learnings with engineering fundamentals.

You can do it too. The key is to not get stuck in the mindset of climbing a ladder. Instead, focus on how you can apply learnings from a separate field into another area.

(A lot of these ideas are covered in David Epstein's book Range which I highly recommend)


  1. In General Game Playing (CS227b at Stanford) Genesereth described a game as strongly winnable if and only if for a given role there is a sequence of individual actions of that role that leads to a [win state]. ↩︎

  2. Future blog post series idea: crafting solutions from problems. ↩︎

  3. Shared vision within a team allows for people to make decisions without additional touchpoints. The decrease in coordination drives more efficient results. ↩︎

  4. In structural engineering, medical devices, and other “real” engineering, this is probably reversed. ↩︎

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